WO1996024637A1 - Verfahren zur herstellung von reaktivazofarbstoffen - Google Patents
Verfahren zur herstellung von reaktivazofarbstoffen Download PDFInfo
- Publication number
- WO1996024637A1 WO1996024637A1 PCT/EP1996/000296 EP9600296W WO9624637A1 WO 1996024637 A1 WO1996024637 A1 WO 1996024637A1 EP 9600296 W EP9600296 W EP 9600296W WO 9624637 A1 WO9624637 A1 WO 9624637A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- compounds
- radical
- acid
- reactive
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- -1 aminoazo Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002790 naphthalenes Chemical class 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 4
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 3
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- DCYBHNIOTZBCFS-UHFFFAOYSA-N 2-amino-5-[(4-sulfophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 DCYBHNIOTZBCFS-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- LAGLYBXIOQLEFA-UHFFFAOYSA-N 2-amino-4-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(S(O)(=O)=O)C(N)=C1 LAGLYBXIOQLEFA-UHFFFAOYSA-N 0.000 description 1
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
- FJHGMUDVUAXUEK-UHFFFAOYSA-N 2-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(N)=C1 FJHGMUDVUAXUEK-UHFFFAOYSA-N 0.000 description 1
- GLABVBIYGGDCNO-UHFFFAOYSA-N 2-amino-5-methoxybenzene-1,4-disulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O GLABVBIYGGDCNO-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- AQKOJKCYBNUFLU-UHFFFAOYSA-N 4,5,6-trifluoropyrimidine Chemical compound FC1=NC=NC(F)=C1F AQKOJKCYBNUFLU-UHFFFAOYSA-N 0.000 description 1
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- GCEGLMFBNPWYQO-UHFFFAOYSA-N 4-fluoro-2,3,5,6-tetrahydroxyhexanal Chemical compound OCC(O)C(F)C(O)C(O)C=O GCEGLMFBNPWYQO-UHFFFAOYSA-N 0.000 description 1
- MBJAPGAZEWPEFB-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O MBJAPGAZEWPEFB-UHFFFAOYSA-N 0.000 description 1
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 1
- DQNOKARDYNQFLN-UHFFFAOYSA-N 5-chloro-4,6-difluoropyrimidine Chemical compound FC1=NC=NC(F)=C1Cl DQNOKARDYNQFLN-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- ZBGXGVYIKJFNAT-UHFFFAOYSA-N 6-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 ZBGXGVYIKJFNAT-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CEYHAERXLATBOK-OSERDNITSA-N Cc(cc(cc(cc1)NC(/C=C\C(O)=O)=O)c1c1O)c1/N=N/c(c(S(O)(=O)=O)c1)ccc1/N=N/c(cc1)ccc1S(O)(=O)=O Chemical compound Cc(cc(cc(cc1)NC(/C=C\C(O)=O)=O)c1c1O)c1/N=N/c(c(S(O)(=O)=O)c1)ccc1/N=N/c(cc1)ccc1S(O)(=O)=O CEYHAERXLATBOK-OSERDNITSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- JBAVAJIXZVRJHT-UHFFFAOYSA-N cresidinesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(C)C=C1N JBAVAJIXZVRJHT-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- FBBHPHRBJLLIFM-UHFFFAOYSA-N pyridin-1-ium-1-carboxylate Chemical compound [O-]C(=O)[N+]1=CC=CC=C1 FBBHPHRBJLLIFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0064—Azodyes with coupling components containing both hydroxyl and amino groups as directing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
Definitions
- the present invention relates to a process for the preparation of reactive azo dyes, starting from maleinylated aminoazo compounds.
- the selectivity of the coupling in the production of azo color substances can be controlled, for example, by parameters such as the temperature and the pH (cf. US Pat. No. 5,350,838).
- DE-A 32 17 224 US-A 4 841 027
- a certain orientation in the coupling is achieved by acylating the amino group of naphthalenesulfonic acid coupling components with an anhydride of a dibasic acid, such as maleic anhydride, before the coupling.
- the aminoazo compounds acylated in this way are then hydrolyzed and temporarily isolated before they are further reacted with reactive components to form reactive dyes.
- a process has now been found for the preparation of reactive azo dyes which, in the form of their free acid, correspond to the formula (I)
- A is the residue of a diazo component, in particular from the benzene or
- X denotes a fiber-reactive heterocyclic radical which is characterized in that maleinylated aminoazo dyes of the formula (IV)
- R 1 and R 2 independently of one another are hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, optionally by substituents such as halogen, in particular F, Cl or Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or SO 3 H, substituted arylazo, especially sulfophenylazo.
- n, o and p are independently 0 or 1.
- R 1 and R 2 independently of one another represent hydrogen, chlorine, fluorine, methyl, ethyl, methoxy, ethoxy or 4-sulfophenylazo.
- the compound obtained in the saponification of the maleinylated aminoazo dye of the formula (IV) probably corresponds to the formula (V)
- A represents a benzene derivative of the formula (II) which corresponds to the formula (VII)
- R 1 , R 2 , n, o or p have the meaning given above
- the saponification is generally carried out in an aqueous alkaline solution, preferably at pH ⁇ 10 and temperatures of 60 ° to 105 ° C; alkali or alkaline earth metal hydroxides are used as bases, preferably sodium hydroxide, potassium hydroxide, lithium hydroxide.
- alkali or alkaline earth metal hydroxides are used as bases, preferably sodium hydroxide, potassium hydroxide, lithium hydroxide.
- the saponification in aqueous-acidic solution is of greater importance, preferably at pH values 4 4 and temperatures of 60 ° to 105 ° C.
- mineral acids are used as acids, preferably hydrochloric acid and Sulfuric acid. Further process parameters for saponification can be found, for example, in DE-A 3 217 224.
- Suitable fiber reactive heterocyclic X i.e. those which react with the OH or NH groups of the fiber under dyeing conditions to form covalent bonds are in particular those which have at least one reactive one
- substituents bound to a 5- or 6-membered aromatic-heterocyclic ring for example to a monoazine, diazine or triazine ring, in particular a pyridine, pyrimidine, pyridazine, pyrazine, thiazine, oxazine or asymmetrical or symmetrical triazine ring, or to such a ring system, which one or more fused aromatic-carbocyclic
- Has rings for example a quinoline, phthalazine, cinnoline, quinazoline, quinoxaline, acridine, phenazine and phenanthridine ring system.
- Fiber-reactive residues from the series of pvrimidines or triazines are particularly suitable.
- the reactive substituents on the heterocycle are, for example, halogen (Cl, Br or F), ammonium including hydrazinium, pyridinium, picolinium, carboxypyridinium, sulfonium, sulfonyl, azido (N 3 ), rhodanido, thiol ether, oxiether, sulfinic acid and sulfonic acid
- X can therefore stand for a radical of the formula
- X-Hal can be mentioned as examples of fiber-reactive radicals
- Ammonia morpholine, aniline, N-methylaniline, N-ethylaniline, o-toluidine, orthanilic acid, metanilic acid, sulfanilic acid, 1, 3-diaminobenzene, 1, 4-diaminobenzene, 2,5-diaminobenzenesulfonic acid, 2,4-diaminobenzenesulfonic acid, 2, 2'-benzidine-disulfonic acid, 1,2-diaminoethane, 1,3-diaminopropane, 1,2-diaminopropane, 4-aminophenyl-ß-sulfatoethylsulfone, 3-aminophenyl-ß-sulfatoethylsulfone, 2-phenylaminoethyl-2'sulfatoethylsulfone, 2 -Phenylaminoethyl-2'2-sulfatoethyl s
- the preferred triazine dyes which are still to be condensed with HR 3 are obtained by the process according to the invention, where X-Hal is cyanuric chloride or cyanuric fluoride.
- the dyes of the formula I obtained by the process according to the invention, in which X is a radical of the formula XV, in which R 3 is F or Cl is and Y, A and m can have the meaning given above, are preferably doubled if they are reacted with diamines, such as those mentioned for HR 3 , These dyes correspond to the formula
- R is a bivalent diamino residue
- a preferred embodiment of the process according to the invention is characterized in that the compounds of the formula (IV) are obtained in that compounds of the formula (XI) or (XII)
- R 1 , R 2 , n, 0 and p have the broadest meaning given above, diazotized and coupled to compounds of the formula (XIII)
- R 1 , R 2 , n, o and p have the broadest meaning mentioned above
- Aminobenzenesulfonic acids of the general formula (XI) are, for example, orthanilic acid, metanilic acid, sulfanilic acid, 2-amino-4-methylbenzenesulfonic acid, 2-amino-4-methoxybenzenesulfonic acid, 2-amino-4-ethoxybenzenesulfonic acid, 4-amino-3-methoxybenzenesulfonic acid Amino-3-methylbenzenesulfonic acid, 4-amino-5-methoxy-2-methylbenzenesulfonic acid, 2-amino-1, 4-benzenedisulfonic acid, 4-amino-1, 3-benzenedisulfonic acid, 2-amino-5-methyl-1,4- benzenedisulfonic acid, 2-amino-5-methoxy-1, 4-benzenedisulfonic acid, 5- (4-sulfophenylazo) -2-aminobenzenesulfonic acid
- Aminonaphthalenesulfonic acids of the general formula (XII) are, for example, 2-amino-1-naphthalenesulfonic acid, 2-amino-1, 5-naphthalenedisulfonic acid, 2-amino-1, 5,7-naphthalenetrisulfonic acid, 3-amino-2,5,7- naphthalenetrisulfonic acid, 3-amino-1, 5-naphthalenedisulfonic acid, 3-amino-1,5,7-naphthalenetrisulfonic acid
- Aminonaphtholsulfonic acid derivatives of the general formula (XIII) are obtained, for example, by reacting maleic anhydride with, for example, 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid, 4-amino-5-hydroxy-1, 7-naphthalenedisulfonic acid.
- maleic anhydride with, for example, 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid, 4-amino-5-hydroxy-1, 7-naphthalenedisulfonic acid.
- 6-amino-4-hydroxy-2-naphthalenesulfonic acid 7-amino-4-hydroxy-2-naphthalenesulfonic acid
- the reaction is described, for example, in DE-A-33 16 984, DE-A-31 18 657 and in EP A 90 1 14 described
- aminobenzene derivatives of the general formula (XI) or the aminonaphthalene derivatives of the general formula (XII) are diazotized by processes known per se by the action of at least one molar equivalent of sodium nitrite in the presence of at least two molar equivalents of a strong acid
- the formulas given are those of free acid.
- the salts are generally obtained in the preparation, in particular the alkali salts such as sodium, potassium or lithium salts
- the reactive dyes produced in this way are ideal for dyeing and printing natural or synthetic hydroxyl or amide groups
- Substrates such as silk, leather, wool, synthetic polyamide fibers, but in particular cellulosic materials with a fibrous structure such as linen, cellulose, regenerated cellulose and especially cotton
- H-acid (1-amino-8-hydroxy-naphthalene-3,6-disulfonic acid) were dissolved in water under protective gas until neutral at a temperature of 20 ° C. 14.7 g of maleic anhydride were added. Value dropped to 4.5 and kept it constant with soda solution, the temperature was kept by external cooling
- Example 2 instead of the H-acid used in Example 1, an aquimolar was used
- Example of use The pH of the solution of the product of the formula (1) obtained in Example 1 was brought to 1.4 with hydrochloric acid, then the mixture was stirred at 70 ° C. for 45 minutes, during which the maleinyl residue was split off. The solution was cooled to 20 ° C. The pH was brought to 3.7 with sodium carbonate solution. After adding 19.6 g of cyanuric chloride, the pH was kept constant with sodium carbonate solution and the temperature was kept constant by external cooling. After the condensation had ended, 6.1 g of 1,4-diaminobenzene were dissolved in water with hydrochloric acid at pH 6 and added to the suspension obtained above. The mixture was heated to 30 ° C., the pH was brought to 6.5 with sodium carbonate solution and held until the reaction had ended. Finally the pH was brought to 8 with sodium carbonate solution, then the dye solution was evaporated to dryness under reduced pressure. 160 g of a dark red powder were obtained, which contained the dye of the formula (8).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96902250A EP0808343B1 (de) | 1995-02-07 | 1996-01-25 | Verfahren zur herstellung von reaktivazofarbstoffen |
| DE59602000T DE59602000D1 (de) | 1995-02-07 | 1996-01-25 | Verfahren zur herstellung von reaktivazofarbstoffen |
| JP8523929A JPH10513495A (ja) | 1995-02-07 | 1996-01-25 | 反応性アゾ染料の製造方法 |
| BR9607112A BR9607112A (pt) | 1995-02-07 | 1996-01-25 | Processo para a preparação de corantes azo reativos |
| US08/875,812 US5872228A (en) | 1995-02-07 | 1996-01-25 | Process for the preparation of reactive azo dyes |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1995103889 DE19503889A1 (de) | 1995-02-07 | 1995-02-07 | Maleinylierte Aminoazoverbindungen |
| DE19527438.5 | 1995-07-27 | ||
| DE1995127438 DE19527438A1 (de) | 1995-07-27 | 1995-07-27 | Verfahren zur Herstellung von Reaktivazofarbstoffen |
| DE19503889.4 | 1995-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996024637A1 true WO1996024637A1 (de) | 1996-08-15 |
Family
ID=26012190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1996/000296 WO1996024637A1 (de) | 1995-02-07 | 1996-01-25 | Verfahren zur herstellung von reaktivazofarbstoffen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5872228A (cs) |
| EP (1) | EP0808343B1 (cs) |
| JP (1) | JPH10513495A (cs) |
| KR (1) | KR19980702000A (cs) |
| CN (1) | CN1173888A (cs) |
| BR (1) | BR9607112A (cs) |
| CA (1) | CA2212143A1 (cs) |
| CZ (1) | CZ251497A3 (cs) |
| DE (1) | DE59602000D1 (cs) |
| WO (1) | WO1996024637A1 (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999058612A1 (de) * | 1998-05-08 | 1999-11-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| CN115521637A (zh) * | 2022-10-09 | 2022-12-27 | 浙江亿得新材料股份有限公司 | 一种复配型浓深艳印花活性大红染料 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9811548D0 (en) * | 1998-05-30 | 1998-07-29 | Clariant Int Ltd | New monoazo dyestuffs |
| KR100812553B1 (ko) * | 2001-06-28 | 2008-03-13 | 스미또모 가가꾸 가부시키가이샤 | 폴리아조 화합물 또는 이의 염과 이를 함유하는 염료계편광막 |
| CN101372467B (zh) * | 2007-08-23 | 2011-09-14 | 明德国际仓储贸易(上海)有限公司 | 具有n,n-二烷氨基的桥基化合物及所应用的染料化合物 |
| CN101565559B (zh) * | 2009-04-14 | 2013-02-13 | 丽源(湖北)科技有限公司 | 一种藏青活性染料混合物及其制备及使用 |
| CN112661888B (zh) * | 2020-12-29 | 2022-05-17 | 科之杰新材料集团浙江有限公司 | 一种减水剂及其制备方法 |
| CN112708074B (zh) * | 2020-12-29 | 2022-05-17 | 科之杰新材料集团浙江有限公司 | 一种聚羧酸减水剂及其制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1934123A1 (de) * | 1968-07-08 | 1970-05-21 | Sumitomo Chemical Co | Monoazoverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung zum Faerben von Textilgut |
| DE3217224A1 (de) * | 1981-05-14 | 1983-01-20 | Sumitomo Chemical Co., Ltd., Osaka | Verfahren zur herstellung von arylazoaminonaphtholsulfonsaeuren, deren verwendung als zwischenprodukte bei der herstellung von reaktivfarbstoffen sowie unter ihrer verwendung hergestellte reaktivfarbstoffe |
| EP0090114A2 (en) * | 1982-03-26 | 1983-10-05 | Imperial Chemical Industries Plc | Reactive dyes |
| EP0406629A2 (de) * | 1989-07-05 | 1991-01-09 | Bayer Ag | Verfahren zur Herstellung von Azofarbstoffen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB988901A (en) * | 1962-01-29 | 1965-04-14 | Ici Ltd | New azo dyestuffs |
| DE3118657A1 (de) * | 1981-05-11 | 1982-11-25 | Basf Ag, 6700 Ludwigshafen | Reaktivfarbstoffe |
| DE3205945A1 (de) * | 1982-02-19 | 1983-09-01 | Hoechst Ag, 6230 Frankfurt | Wasserloesliche disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| JPS59122549A (ja) * | 1982-12-28 | 1984-07-16 | Sumitomo Chem Co Ltd | 新規なモノアゾ化合物 |
| DE3316984A1 (de) * | 1983-05-10 | 1984-11-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von o-sulfonsaeureestern gegebenenfalls substituierter aminonaphthole |
| US5350838A (en) * | 1993-02-08 | 1994-09-27 | Hoechst Celanese Corporation | High temperature process for preparing fiber reactive dyes |
| DE4314300A1 (de) * | 1993-04-30 | 1994-11-03 | Bayer Ag | Reaktivfarbstoffe |
-
1996
- 1996-01-25 DE DE59602000T patent/DE59602000D1/de not_active Expired - Fee Related
- 1996-01-25 KR KR1019970705397A patent/KR19980702000A/ko not_active Withdrawn
- 1996-01-25 BR BR9607112A patent/BR9607112A/pt not_active Application Discontinuation
- 1996-01-25 CA CA002212143A patent/CA2212143A1/en not_active Abandoned
- 1996-01-25 US US08/875,812 patent/US5872228A/en not_active Expired - Fee Related
- 1996-01-25 EP EP96902250A patent/EP0808343B1/de not_active Expired - Lifetime
- 1996-01-25 CZ CZ972514A patent/CZ251497A3/cs unknown
- 1996-01-25 WO PCT/EP1996/000296 patent/WO1996024637A1/de not_active Application Discontinuation
- 1996-01-25 JP JP8523929A patent/JPH10513495A/ja active Pending
- 1996-01-25 CN CN96191812A patent/CN1173888A/zh active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1934123A1 (de) * | 1968-07-08 | 1970-05-21 | Sumitomo Chemical Co | Monoazoverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung zum Faerben von Textilgut |
| DE3217224A1 (de) * | 1981-05-14 | 1983-01-20 | Sumitomo Chemical Co., Ltd., Osaka | Verfahren zur herstellung von arylazoaminonaphtholsulfonsaeuren, deren verwendung als zwischenprodukte bei der herstellung von reaktivfarbstoffen sowie unter ihrer verwendung hergestellte reaktivfarbstoffe |
| GB2103232A (en) * | 1981-05-14 | 1983-02-16 | Sumitomo Chemical Co | Arylazo-aminonaphtholsulfonic acid |
| US4841027A (en) * | 1981-05-14 | 1989-06-20 | Sumitomo Chemical Company, Limited | Process for preparing phenyl- and naphthylazo-aminonaphthol sulphonic acids |
| EP0090114A2 (en) * | 1982-03-26 | 1983-10-05 | Imperial Chemical Industries Plc | Reactive dyes |
| EP0406629A2 (de) * | 1989-07-05 | 1991-01-09 | Bayer Ag | Verfahren zur Herstellung von Azofarbstoffen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999058612A1 (de) * | 1998-05-08 | 1999-11-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| CN115521637A (zh) * | 2022-10-09 | 2022-12-27 | 浙江亿得新材料股份有限公司 | 一种复配型浓深艳印花活性大红染料 |
| CN115521637B (zh) * | 2022-10-09 | 2023-08-08 | 浙江亿得新材料股份有限公司 | 一种复配型浓深艳印花活性大红染料 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5872228A (en) | 1999-02-16 |
| EP0808343B1 (de) | 1999-05-26 |
| CZ251497A3 (cs) | 1998-03-18 |
| DE59602000D1 (de) | 1999-07-01 |
| CN1173888A (zh) | 1998-02-18 |
| CA2212143A1 (en) | 1996-08-15 |
| KR19980702000A (ko) | 1998-06-25 |
| BR9607112A (pt) | 1997-11-04 |
| JPH10513495A (ja) | 1998-12-22 |
| EP0808343A1 (de) | 1997-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH622818A5 (en) | Process for the preparation of novel reactive dyestuffs | |
| DE2653199C2 (cs) | ||
| EP0497174B1 (de) | Vinylsulfon/Pyrimidingruppenhaltige bifunktionelle Reaktivfarbstoffe | |
| EP0159292A2 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
| EP0084314B1 (de) | Disazoreaktivfarbstoffe | |
| EP0808343B1 (de) | Verfahren zur herstellung von reaktivazofarbstoffen | |
| DE2913102C2 (de) | 5-Aminomethyl-2-aminonaphthalin-7-sulfonsäure-Derivate, deren Herstellung und Verwendung | |
| DE2903594A1 (de) | Fluortriazin-reaktivfarbstoffe und verfahren zur herstellung von fluortriazin-derivaten | |
| EP0001629B1 (de) | Wasserlösliche, faserreaktive grüne Phthalocyanin-Azofarbstoffe, ihre Herstellung und ihre Verwendung | |
| EP0962500A1 (de) | Wasserlösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe | |
| EP0001451B1 (de) | Wasserlösliche faserreaktive grüne Phthalocyanin-Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0213071B1 (de) | Verfahren zur Herstellung faserreaktiver Azoverbindungen | |
| CH624426A5 (en) | Process for preparing reactive azo dyes | |
| DE2729240A1 (de) | Azo-reaktivfarbstoffe | |
| DE3039137C2 (cs) | ||
| DE19527438A1 (de) | Verfahren zur Herstellung von Reaktivazofarbstoffen | |
| DE69803988T2 (de) | Reaktive diamin-verknüpfte azofarbstoffe | |
| EP0641838A1 (de) | Reaktivfarbstoffe auf Basis einer substituierten Barbitursäure | |
| DE19503889A1 (de) | Maleinylierte Aminoazoverbindungen | |
| DE2924000C2 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
| DE2746441A1 (de) | Faserreaktive phthalocyaninazofarbstoffe | |
| DE2733109C2 (de) | Faserreaktive Disazofarbstoffe, deren Herstellung und Verwendung | |
| WO1991009913A1 (de) | Azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe | |
| DE3800692A1 (de) | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe | |
| EP0068153B1 (de) | Faserreaktive Disazofarbstoffe, ihre Herstellung und Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WWE | Wipo information: entry into national phase |
Ref document number: 96191812.8 Country of ref document: CN |
|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): BR CA CN CZ JP KR LT PL SI US |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| WWE | Wipo information: entry into national phase |
Ref document number: 1996902250 Country of ref document: EP |
|
| ENP | Entry into the national phase |
Ref document number: 2212143 Country of ref document: CA Ref document number: 2212143 Country of ref document: CA Kind code of ref document: A Ref document number: 1996 523929 Country of ref document: JP Kind code of ref document: A |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 08875812 Country of ref document: US |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 1019970705397 Country of ref document: KR |
|
| WWE | Wipo information: entry into national phase |
Ref document number: PV1997-2514 Country of ref document: CZ |
|
| WWP | Wipo information: published in national office |
Ref document number: 1996902250 Country of ref document: EP |
|
| WWP | Wipo information: published in national office |
Ref document number: PV1997-2514 Country of ref document: CZ |
|
| WWP | Wipo information: published in national office |
Ref document number: 1019970705397 Country of ref document: KR |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: PV1997-2514 Country of ref document: CZ |
|
| WWG | Wipo information: grant in national office |
Ref document number: 1996902250 Country of ref document: EP |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: 1019970705397 Country of ref document: KR |